On the trailer with the bilge dry and the drain plug removed, run the engine on muffs looks for water to exit the drain hole. If it leaks with the motor running:
Y pipe, cracked block, split hose, loose hose clamp
If no leaks, leave boat attached to trailer and lower slowly down the ramp untill the leak appears,grease pencil the waterline on the hull. pull up from the ramp and look at everything below that level. Hoses, clamps, boot/bellows, transom, corrosion,etc.
post the results
I think the ramp and the grease pencil idea is a good contribution to troubleshooting this problem.
I love these forums cause you can always learn a new trick from someone somewhere.